chatham real estate
An unpretentious approach to buying and selling with a broker who brings 30 years of construction and management experience to the process.
”BY FAR the best experience we’ve ever had. He is unlike anyone in the business. He has broken the mold of what we know to be the real estate brokerage business.” Maura Fitzpatrick . Orleans
“We recently worked with Jon, and it was, BY FAR, the best experience we have ever had. This was our 10th real estate transaction, and we had been completely underwhelmed by the real estate industry to date. It has felt like a very transactional business, lacking the personal touch, honesty and accountability that you would expect for such a personal and emotional experience. Jon changed all that. He is unlike anyone in the business from both a personal and emotional standpoint. On a personal level, there is no outer shell, you know what you are getting from the minute you meet him. Not only does this make for a pleasant experience, but when things get difficult, as they inevitably will during a transaction, knowing who you are dealing with, and that you can trust Jon, is invaluable. On a professional level, he has broken the mold of what we know to be the real estate brokerage business. Take a read through his website, about covering innocuous fees, coordinating cleanouts, taking care of things that he doesn’t want credit for and you only find out about later….it’s all true. If you want an experience where your opinion is important, where you can trust the process and feel really good at the end, you should reach out to Jon. It was such a good experience that I now consider Jon a friend and will go out of my way every chance I get to find him more business.”
Active Chatham Listings
- 912 Main Street Unit 308
- Chatham MA 02633
- $459,000
- 1 Beds | 2 Baths | 1,284 SqFt
- 0 Acres
- 1 Peirce Path South
- Chatham MA 02659
- $4,499,900
- 3 Beds | 6 Baths | 4,450 SqFt
- 0.7 Acres
- 1772 Main Street
- Chatham MA 02633
- $700,000
- Beds | 0.5 Baths | 600 SqFt
- 0.17 Acres
- 169 Tisquantum Road
- Chatham MA 02633
- $5,400,000
- 5 Beds | 4.5 Baths | 5,587 SqFt
- 1.14 Acres
- 32 Gladen Lane
- Chatham MA 02633
- $2,850,000
- 3 Beds | 3 Baths | 1,999 SqFt
- 0.51 Acres
- 70 Old Queen Anne Road
- Chatham MA 02633
- $1,795,000
- 3 Beds | 3.5 Baths | 2,248 SqFt
- 0.56 Acres
- 197 Woodland Way North
- Chatham MA 02650
- $10,995,000
- 6 Beds | 5.5 Baths | 6,547 SqFt
- 1.33 Acres
- 42 Champlain Road
- Chatham MA 02633
- $1,800,000
- 4 Beds | 2 Baths | 1,435 SqFt
- 0.34 Acres
- 118 Wilfred Road
- Chatham MA 02633
- $1,200,000
- 3 Beds | 3 Baths | 1,804 SqFt
- 0.34 Acres
- 46 Chippingstone Road
- Chatham MA 02633
- $919,000
- 3 Beds | 2 Baths | 1,713 SqFt
- 0 Acres
- 222 Barcliff Avenue
- Chatham MA 02633
- $4,250,000
- 4 Beds | 5.5 Baths | 3,980 SqFt
- 0.47 Acres
- 50 Eldredge Square S
- Chatham MA 02633
- $1,995,000
- 3 Beds | 2 Baths | 1,488 SqFt
- 0.23 Acres
- 2548 Main Street South
- Chatham MA 02659
- $3,999,900
- 4 Beds | 5.5 Baths | 4,942 SqFt
- 0.85 Acres
- 66 Ethelma Drive
- Chatham MA 02633
- $949,000
- 4 Beds | 1 Baths | 1,547 SqFt
- 0.55 Acres
- 234 Round Cove Road
- Chatham MA 02633
- $2,150,000
- 3 Beds | 2.5 Baths | 2,481 SqFt
- 0.51 Acres
- 38 Indian Trail
- Chatham MA 02633
- $4,750,000
- 4 Beds | 3.5 Baths | 4,967 SqFt
- 1.38 Acres
- 16 Old Salt Works Road
- Chatham MA 02633
- $2,500,000
- 3 Beds | 2.5 Baths | 2,426 SqFt
- 0.49 Acres
- 29 Jessies Landing
- Chatham MA 02633
- $3,699,900
- 3 Beds | 4.5 Baths | 4,565 SqFt
- 0.46 Acres
- 298 Chippingstone Road
- Chatham MA 02633
- $1,050,000
- 4 Beds | 2 Baths | 2,148 SqFt
- 0.46 Acres
- 287 Cedar Street
- Chatham MA 02633
- $3,850,000
- 3 Beds | 4.5 Baths | 3,640 SqFt
- 0.35 Acres
- 27 Martha Kendrick Drive
- Chatham MA 02633
- $1,200,000
- 3 Beds | 2.5 Baths | 2,066 SqFt
- 0.36 Acres
- 100 Heritage Lane
- Chatham MA 02633
- $599,000
- 4 Beds | 1.5 Baths | 1,144 SqFt
- 0.36 Acres
- 92 Absegami Run
- Chatham MA 02633
- $3,699,900
- 4 Beds | 3.5 Baths | 3,199 SqFt
- 0.57 Acres
- 48 Sylvan Way South
- Chatham MA 02659
- $4,999,000
- 6 Beds | 6 Baths | 5,721 SqFt
- 1.63 Acres
Chatham Mass Real Estate
Often penned from a local perspective as a quaint drinking village with a fishing problem, Chatham, situated on the elbow of the Cape, settled in 1664, offers something for everyone. If you can’t find it in one of the locally owned shops dotted up and down what is arguably the most genuine and authentic Main Street amongst each of the lower and outercape towns, Chatham hosts a variety of top-end eateries, Band Concert, as well The Chatham Angler’s of the famed Cape Cod Baseball League.
Chatham real estate no doubt leans toward the top end of the charts in terms of pricing. Although you should never rule out finding that diamond in the rough, price points over $1 million and perhaps $2 million, inventory in the Chatham real estate pool routinely outweighs comparative value options in the sub $1 million range.
One More Chatham fun fact: Replaced by conventional steel and concrete in 2014, The Mitchell River Bridge, an iconic piece of Chatham real estate, would be the last wooden drawbridge in the United States.

